Events in Plymouth, WI

● Listings verifiedThursday, September 17 · every listing checked against its source by our Plymouth editors

35This week
87Next 30 days
5Free this week
65Venues tracked

This weekend in Plymouth

The ones worth planning around. All 14 weekend events →

Cars & Coffee

Sat, Sep 19 · 8:30am · Kennedy Ford, Sheboygan Falls

Free events in Plymouth

5 of this week's 35 events cost nothing. See all 5 free events →

  • Thu 3pm

    Plymouth Farmers and Artisan Market: Weekly Thursdays June-October

    STAYER PARK, 39 South Stafford Street, Plymouth, WI, United States, Wisconsin 53073, 15 S Stafford St, Plymouth · verified Sep 13
    Free

    The Plymouth Farmers Market returns to Stayer Park, creating a welcoming weekly marketplace for the community. Vendor and musician lineups are posted on the market’s main page throughout the season. Prospective vendors must apply only through the official application portal. Do not submit applications via Facebook or send payments to individuals, as commenters do not represent the market. Nourish Farms, a 501c3, serves as the market’s nonprofit agent, supporting good food education, school and community programs for all ages, and opportunities to volunteer and get involved. The market is presented with support from the City of Plymouth.

    Event website ↗
  • Fri 9am

    Rock the Block 2026: End Park Neighborhood

    End Park, 1236 Bell Ave, Sheboygan · verified Sep 13
    Free

    Habitat for Humanity Lakeside is bringing its annual neighborhood revitalization to Sheboygan’s End Park area. The effort focuses on small exterior tasks for homeowners within the boundaries of Main Ave to the north, Geele Ave to the south, 10th St to the east, and 15th St to the west. Projects may include porch repair and painting, yard cleanup, repairs to exterior doors and windows, simple fixes to outdoor lighting or fixtures without new wiring, and light landscaping. Sponsorship opportunities for Rock the Block are available to Sheboygan businesses at a range of levels, each offering its own perks.

    Event website ↗
  • Sat 8am

    SCIO Sheboygan Summer Market Fountain

    Fountain Park - Sheboygan, Sheboygan · verified Sep 13
    Free

    At historic Fountain Park, the SCIO Sheboygan Summer Farmers Market highlights the flavors and makers of Wisconsin. Browse stalls filled with seasonal produce, locally raised meats, eggs, cheeses, and fresh-baked treats, along with flowers, food trucks, and artisan crafts from vendors within 100 miles. FoodShare and EBT shoppers can visit the SCIO Information Booth to use their card and receive Double Your Bucks, matching up to $20 per day on fresh fruits and vegetables. WIC and SFMNP vouchers are also accepted.

    Event website ↗
  • Sat 9am

    Kiel Shred Event

    110 Fremont St, Kiel · verified Sep 13
    Free

    Bank First presents a free community paper shredding event that helps residents safeguard personal information while supporting neighbors in need. The service is open to all, and participants are asked to bring one nonperishable food donation for each bag of personal documents they plan to shred. All donated food goes to area pantries. Shredding is performed on site by Confidential Records, an AAA certified provider that deploys mobile units and employs licensed, bonded specialists. They ensure secure handling and removal of all shredded material, and attendees may watch the process for added peace of mind. The event will take place rain or shine, and to leave room for households, businesses are asked not to participate. Acceptable items include sensitive papers such as old tax returns, bank and credit card statements, medical records and similar personal documents. Items that cannot be accepted include black butterfly clips, hanging file folders, three ring binders, hard drives, magnetic tapes and plastic items. Previous rounds of this program have processed 87,600 pounds of paper across 18 events, followed by 91,975 pounds across 20 locations, reflecting strong community participation in secure document disposal.

    Event website ↗

Live music in Plymouth

8 shows this weeksee the full live-music calendar →

  • Thu 6pm

    Open Jam Thursdays

    N7454 Summit Road, Plymouth, WI, United States, Wisconsin 53073, Plymouth · verified Sep 13
    See details

    This open jam welcomes musicians at any stage of experience. Available to use are a bass guitar with amplifiers, a keyboard, an accordion, and a drum kit. It offers a friendly space to play, collaborate, and enjoy making music with others.

    Event website ↗
  • Fri 7pm

    Getting you shaking your groove thing

    Rumors Roadhouse, Plymouth · verified Sep 13
    See details

    Settle in with smoked meats and a couple of cold beers, then head to the floor to show off your best moves. A simple, feel good mix of tasty bites, refreshing drinks, and dancing.

    Event website ↗
  • Fri 8pm

    Karaoke at Uncle Gunters

    Uncle Gunters, 418 Broadway St, Sheboygan Falls · verified Sep 13
    See details

    Karaoke takes center stage at Uncle Gunter's, a spot with Wisconsin charm, craft cocktails, and satisfying bites. Sip an Old Fashioned, pair it with a gourmet panini or classic cheese curds, then step up to the mic for your favorite tunes. The cozy, welcoming atmosphere makes it an easy place to unwind between songs.

    Event website ↗
  • Sat 11am

    River Fest

    Parker John's BBQ & Pizza, 705 Riverfront Dr, Sheboygan · verified Sep 13
    See details

    Sheboygan residents and visitors converge for a one-day celebration of music, food, and family activities along the Riverfront Drive Boardwalk. The lineup includes live performances by the Minor Worries and Buffalo Joe bands, appearances by the Balloon Lady and children’s entertainer Randy Peterson, more activities for children, vendor booths showcasing local businesses, a fashion walk, food trucks, and additional attractions. Presented by the Harbor Centre Business District.

    Event website ↗

All upcoming events, day by day

Every event we track in Plymouth this week, in order. After one kind of thing? Live music and family events have their own calendars.

Thursday, September 17 4 events
  • 3pm

    Plymouth Farmers and Artisan Market: Weekly Thursdays June-October

    STAYER PARK, 39 South Stafford Street, Plymouth, WI, United States, Wisconsin 53073, 15 S Stafford St, Plymouth · verified Sep 13
    Free

    The Plymouth Farmers Market returns to Stayer Park, creating a welcoming weekly marketplace for the community. Vendor and musician lineups are posted on the market’s main page throughout the season. Prospective vendors must apply only through the official application portal. Do not submit applications via Facebook or send payments to individuals, as commenters do not represent the market. Nourish Farms, a 501c3, serves as the market’s nonprofit agent, supporting good food education, school and community programs for all ages, and opportunities to volunteer and get involved. The market is presented with support from the City of Plymouth.

    Event website ↗
  • 4pm

    LEGO Club

    130 Division St, Plymouth · verified Sep 13
    See details

    An open-house LEGO Club at the library welcomes children ages 6 to 11. Kids can stretch their creativity and building skills, exchange ideas, collaborate on creations, and make new friends. A caregiver needs to stay in the building with children under 10. Friends are welcome, and no registration is required.

    Event website ↗
  • 5pm

    Garden Riot Pop Up

    Harvest Street Garage 1821 Cooper Ave Sheboygan, 1821 Cooper Ave, Sheboygan · verified Sep 13
    See details

    This one-night pop up at Harvest Street Garage centers on fresh, local produce. The Garden Riot menu features vegetarian and vegan dishes made with ingredients from local farms and will be available only during this event. Outdoor seating is limited to 20, and ADA seating is available. If the weather turns, convenient to-go bags can be provided. Street parking is requested.

    Event website ↗
  • 6pm

    Open Jam Thursdays

    N7454 Summit Road, Plymouth, WI, United States, Wisconsin 53073, Plymouth · verified Sep 13
    See details

    This open jam welcomes musicians at any stage of experience. Available to use are a bass guitar with amplifiers, a keyboard, an accordion, and a drum kit. It offers a friendly space to play, collaborate, and enjoy making music with others.

    Event website ↗
Friday, September 18 5 events
  • 7am

    Art on Wheels Vintage Weekend with VSCDA

    Road America, Plymouth · verified Sep 13
    See details

    Art on Wheels Vintage Weekend with VSCDA celebrates the heritage of vintage racing with three days of on track excitement at Road America. More than 300 carefully restored historic race cars across 11 classes take to the famed circuit, creating a moving showcase of automotive history from graceful classic sports cars to the raw punch of muscle machines. Spectators can enter the paddock, see the cars up close in their period-correct preparation, and observe the skill and craftsmanship that keep these treasured racers ready to run.

    Event website ↗
  • 9am

    Rock the Block 2026: End Park Neighborhood

    End Park, 1236 Bell Ave, Sheboygan · verified Sep 13
    Free

    Habitat for Humanity Lakeside is bringing its annual neighborhood revitalization to Sheboygan’s End Park area. The effort focuses on small exterior tasks for homeowners within the boundaries of Main Ave to the north, Geele Ave to the south, 10th St to the east, and 15th St to the west. Projects may include porch repair and painting, yard cleanup, repairs to exterior doors and windows, simple fixes to outdoor lighting or fixtures without new wiring, and light landscaping. Sponsorship opportunities for Rock the Block are available to Sheboygan businesses at a range of levels, each offering its own perks.

    Event website ↗
  • 5:30pm

    Pasta II | Cooking School

    101 Osthoff Ave, Elkhart Lake · verified Sep 13
    See details

    Dive into the craft of handmade pasta in an interactive cooking class guided by a professional chef. Roll fresh dough and create two dishes, salmon and asparagus linguine and mushroom ravioli finished with sage and brown butter. Each attendee receives two complimentary beverages. The cost is $79 per person, plus tax and fees. Tickets are non-refundable.

    Event website ↗
  • 7pm

    Getting you shaking your groove thing

    Rumors Roadhouse, Plymouth · verified Sep 13
    See details

    Settle in with smoked meats and a couple of cold beers, then head to the floor to show off your best moves. A simple, feel good mix of tasty bites, refreshing drinks, and dancing.

    Event website ↗
  • 8pm

    Karaoke at Uncle Gunters

    Uncle Gunters, 418 Broadway St, Sheboygan Falls · verified Sep 13
    See details

    Karaoke takes center stage at Uncle Gunter's, a spot with Wisconsin charm, craft cocktails, and satisfying bites. Sip an Old Fashioned, pair it with a gourmet panini or classic cheese curds, then step up to the mic for your favorite tunes. The cozy, welcoming atmosphere makes it an easy place to unwind between songs.

    Event website ↗
Saturday, September 19 11 events
  • 8am

    SCIO Sheboygan Summer Market Fountain

    Fountain Park - Sheboygan, Sheboygan · verified Sep 13
    Free

    At historic Fountain Park, the SCIO Sheboygan Summer Farmers Market highlights the flavors and makers of Wisconsin. Browse stalls filled with seasonal produce, locally raised meats, eggs, cheeses, and fresh-baked treats, along with flowers, food trucks, and artisan crafts from vendors within 100 miles. FoodShare and EBT shoppers can visit the SCIO Information Booth to use their card and receive Double Your Bucks, matching up to $20 per day on fresh fruits and vegetables. WIC and SFMNP vouchers are also accepted.

    Event website ↗
  • 8am

    Road America AutoCross Series 9/19/2026

    Road America, Plymouth · verified Sep 13
    See details

    The Road America AutoCross Series brings timed competition to the Briggs & Stratton Motorplex at America’s National Park of Speed, powered by FVSCC. Drivers race the clock on a course that evolves from event to event, emphasizing precision, car control, and quick decision-making. SCCA classes and autocross rules govern the action, cars must pass a basic safety inspection, and a DOT-rated helmet is required. The day typically flows with check-in, a course walk, tech inspection, a drivers meeting, timed runs, and awards to wrap things up. Entry is $75 and the field is capped at 150 drivers. Each driver entry includes admission for two spectators when they arrive with the driver. Spectator admission is $10, and kids 16 and under are free. Food will be available for purchase at the Road America concession stand. The series contributes to FVSCC season points and will crown its own champion across multiple events.

    Event website ↗
  • 8:30am

    Cars & Coffee

    Kennedy Ford, 348 Monroe St, Sheboygan Falls · verified Sep 13
    See details

    A relaxed morning gathering for car enthusiasts where participants bring their ride to spend time together. Coffee, water, and doughnuts are provided.

    Event website ↗
  • 9am

    Kiel Shred Event

    110 Fremont St, Kiel · verified Sep 13
    Free

    Bank First presents a free community paper shredding event that helps residents safeguard personal information while supporting neighbors in need. The service is open to all, and participants are asked to bring one nonperishable food donation for each bag of personal documents they plan to shred. All donated food goes to area pantries. Shredding is performed on site by Confidential Records, an AAA certified provider that deploys mobile units and employs licensed, bonded specialists. They ensure secure handling and removal of all shredded material, and attendees may watch the process for added peace of mind. The event will take place rain or shine, and to leave room for households, businesses are asked not to participate. Acceptable items include sensitive papers such as old tax returns, bank and credit card statements, medical records and similar personal documents. Items that cannot be accepted include black butterfly clips, hanging file folders, three ring binders, hard drives, magnetic tapes and plastic items. Previous rounds of this program have processed 87,600 pounds of paper across 18 events, followed by 91,975 pounds across 20 locations, reflecting strong community participation in secure document disposal.

    Event website ↗
  • 9am

    There is HOPE Suicide Awareness Walk

    Deland Park, 913 Broughton Dr, Sheboygan · verified Sep 13
    See details

    An annual community walk along the Lake Michigan shoreline in Sheboygan, Wisconsin raises funds and advances suicide awareness. It honors those grieving a loss to suicide and brings people together to make a difference. The gathering also provides a supportive setting for individuals facing mental health challenges to encourage one another and feel the care of the wider community. All proceeds support programming focused on mental health and suicide prevention. Details about registration and sponsorship will be available soon.

    Event website ↗
  • 9:30am

    Prairie Schooner Saturdays

    W7965 State Highway 23, Greenbush, WI, United States, Wisconsin 53026, Glenbeulah · verified Sep 13
    See details

    Travel the Kettle Moraine landscape in a horse-drawn covered wagon crafted by Hansen Wheel & Wagon Shop and finished in period-correct colors, offering a vivid look at how families like Laura Ingalls Wilder’s moved around the Midwest in the 1800s. The experience features nine scheduled rides, each about 30 minutes, and tickets correspond to a specific departure. The wagon ride is just one part of a broader visit to the Wade House Historic Site, where the Wesley W. Jung Carriage Museum showcases Wisconsin’s largest collection of historic carriages and wagons. Explore the restored Stagecoach Inn, visit the sawmill and blacksmith shop to learn about period trades, and take advantage of horse-drawn transport between the visitor center and the historic core. All guests check in at the Visitor Center for a required safety briefing before boarding. Rides may be canceled and fully refunded in the event of severe weather. Parking, restrooms, and beverages are available. The Visitor Center is ADA compliant and includes elevator access, and guests with additional mobility needs are encouraged to contact the site. Pricing is as follows: Adults 18–64 and Teens 13–17 at 15, Seniors 65+ at 13, Children 5–12 at 10, and Children under 5 at 3. Society members receive a 10 percent discount. General admission is an additional cost, with tickets available online or onsite.

    Event website ↗
  • 11am

    River Fest

    Parker John's BBQ & Pizza, 705 Riverfront Dr, Sheboygan · verified Sep 13
    See details

    Sheboygan residents and visitors converge for a one-day celebration of music, food, and family activities along the Riverfront Drive Boardwalk. The lineup includes live performances by the Minor Worries and Buffalo Joe bands, appearances by the Balloon Lady and children’s entertainer Randy Peterson, more activities for children, vendor booths showcasing local businesses, a fashion walk, food trucks, and additional attractions. Presented by the Harbor Centre Business District.

    Event website ↗
  • 1pm

    Open for Tours

    1600 Wisconsin Ave, New Holstein · verified Sep 13
    See details

    Step inside the Timm House for a docent-led walk through both floors, featuring stories about the Timm family and everyday life in New Holstein. Continue your history outing at The Pioneer Corner Museum, where you can explore the exhibits at your own pace. Knowledgeable docents are available to answer questions. Admission is $7 for adults and $3 for children at each site. Combination tickets to experience both locations are $10 for adults and $5 for children, and they do not have to be used on the same day. Tickets can be purchased at the door or through the ticket link in this event.

    Event website ↗
  • 4pm

    LIVE AT SOLU - The LoveMonkeys 9-19-2026

    SoLu Estate Winery, Cascade · verified Sep 13
    See details

    The LoveMonkeys bring a high-energy mix of rock, pop, and reggae to SoLu Estate Winery, showcasing the creativity and spark that have driven the band for more than 30 years. Known in the Midwest for a distinctive live show, they continue to attract large crowds and keep the momentum strong. There is a $10 cover, and tickets are required, available online or at the door. Optional table reservations include guaranteed seating, a drink ticket for each guest, an admission ticket for each guest, and a prime view of the band.

    Event website ↗
  • 4:30pm

    Pasta II | Cooking School

    101 Osthoff Ave, Elkhart Lake · verified Sep 13
    See details

    Roll up your sleeves for a hands-on pasta workshop guided by a professional chef. Learn to mix and knead fresh dough, then create two dishes... salmon and asparagus linguine, plus mushroom ravioli finished with sage and browned butter. Each attendee receives two complimentary beverages. Cost is $79 per person, with tax and fees additional. Tickets cannot be refunded.

    Event website ↗
  • 7pm

    Barefoot Americans doing a solo thing

    N7454 Summit Road, Plymouth, WI, Plymouth · verified Sep 13
    See details

    Settle in with a beverage and some tasty BBQ as Barefoot Americans takes the stage for a solo set of lively ukulele tunes. The easygoing vibe and upbeat melodies offer feel-good sounds made for unwinding and lifting the spirit.

    Event website ↗
Sunday, September 20 3 events
  • 1pm

    Wisconsin Seasons at Wolf and Fox Winery

    W1139 Lime Kiln Rd, New Holstein, WI 53061-9724, United States, New Holstein · verified Sep 13
    See details

    Unwind with an afternoon of painting at Wolf and Fox Winery, where certified art instructor Miki Wise guides a Wisconsin-themed canvas from start to finish with easy, step-by-step instruction. No experience is needed. A Wisconsin-shaped stencil is provided, and you can personalize the piece by swapping the seasonal elements for your favorite sports team logos if you prefer. All materials and tools are included. Beverages and snacks are available for purchase from the winery. The cost is $35 per person, payable by cash, check, or Venmo. To reserve a spot or ask questions, call Wolf and Fox Winery at (920) 522-3196 or email Miki at dansenqueen@hotmail.com.

    Event website ↗
  • 1pm

    12 SPOTS LEFT! Sept 20th - Rumors Roadhouse Chunky Knit Blanket Workshop

    Rumors Roadhouse, Plymouth · verified Sep 13
    See details

    At Rumors Roadhouse, this hands-on workshop teaches participants to create a chunky knit blanket using only their hands, with food and drinks as part of the experience. It welcomes complete beginners and seasoned knitters alike. Everyone finishes a cozy blanket to take home in a blanket bag and later receives emailed instructions and yarn shopping tips for future projects. Blanket size varies based on how tight or loose you choose to knit. A very tight knit typically measures about 45 by 42 inches, and most turn out larger. Pre-registration is required, and seating is limited on a first come, first served basis. Two pricing options are offered. The $65 option allows you to pick from the yarn colors brought to the workshop. The $85 option lets you preselect one or two colors from a premium, softer, thicker yarn that tends to hide imperfections, with a color selection email sent about four weeks before the workshop. Registration for the $85 option closes four weeks prior if not sold out, and the $65 option closes two weeks prior. Participants ages 12 and up may work independently on a blanket. Apple Pay may not work well with the booking system. If you want the social experience without the knitting, an optional $35 add-on can have your blanket completed ahead of time and ready for you at the workshop when purchased at least two weeks beforehand. This add-on is available only with the $85 registration.

    Event website ↗
  • 3pm

    Dylan Michael @ Edgewater Bar & Grill

    Edgewater Bar & Grill, 509 5th St, Kiel · verified Sep 13
    See details

    Dylan Michael brings an acoustic duo to Edgewater Bar & Grill for his first appearance at the venue, joined by guitarist JJ Lukas. The set blends country and southern rock with well-known tunes, all delivered in a relaxed, stripped-down style suited for an easygoing afternoon.

    Event website ↗
Monday, September 21 4 events
  • 6:30am

    MotoVid - RIDE Road America - All Levels Track Days

    Road America, Plymouth · verified Sep 13
    See details

    Motovid.com brings its All Levels Track Day program back to the Road America circuit for two rounds. The established format places riders into four experience-based groups: Blue for advanced, Green for intermediate 1, Orange for intermediate 2, and Yellow for novice. Each group takes to the track on the hour with assigned CRs, creating a setting designed to be conducive for participants at every skill level on the big track.

    Event website ↗
  • 5:30pm

    Sheboygan, WI Ruby’s Pantry – Stretch Your Grocery Budget

    Emil Mazey Hall, 5425 Superior Ave, Sheboygan · verified Sep 13
    See details

    Ruby’s Pantry presents a community grocery distribution in Sheboygan at Emil Mazey Hall. For a $30 contribution, participants receive a grocery bundle. There are no income or residency restrictions, so everyone is welcome to take part. The assortment can change, but the aim is to provide solid value. If you receive items you will not use, consider sharing them with a neighbor to brighten someone else’s day.

    Event website ↗
  • 6pm

    RL Garden Club Monthly Meeting

    The Random Cup, 430 1st St, Random Lake · verified Sep 13
    See details

    The Random Lake Garden Club hosts a monthly meeting at The Random Cup. Attendees connect over gardening, share ideas, and learn from one another while coordinating efforts that benefit the Village of Random Lake. The club plants and cares for local gardens and organizes fundraisers that support community plantings and beautification projects. The meeting is open to all.

    Event website ↗
  • 6pm

    4 Miles of Fitness

    Road America, Plymouth · verified Sep 13
    See details

    Ride a bike, take a walk, or go for a run at Road America on an iconic four-mile circuit with 14 turns. Beyond the main track, the experience extends to cross-country paths and service roads across the 640-acre property, providing a traffic-free setting away from neighborhood distractions. Pets, scooters, and skateboards are not permitted. Entry is $5 per person at the gate, cash only, with options for an eight-visit pass at $25 or an unlimited season membership for $60. Groups of 10 or more qualify for discounts, and youth ages 16 and under are admitted free when accompanied by an adult. All participants must complete the Speed Pass waiver prior to arrival.

    Event website ↗
Tuesday, September 22 5 events
  • 7:45am

    Road America HPDE Track Event: Chin Track Days

    Road America, Plymouth · verified Sep 13
    See details

    Road America returns to the Chin Track Days schedule with a two-day HPDE at a celebrated American road course. Photo credit goes to Edmund.

    Event website ↗
  • 3pm

    Ecstatic Dance Tuesdays

    Uptown Social , 1817 N 8th St, Sheboygan · verified Sep 15
    See details

    An hour of ecstatic dance open to everyone at Uptown Social. Non-members can check in at the front desk, then head to the dance and exercise room. A $5 cash contribution per session supports facilitators Jokasha and Kathy.

    Event website ↗
  • 5pm

    HGFD Bingo

    Howards Grove Fire Department, 958 S Wisconsin Dr, Sheboygan · verified Sep 15
    See details

    Now in its third season, HGFD Bingo returns with another round of play. Doors will open before play begins. Additional details will be announced.

    Event website ↗
  • 5:30pm

    Tuesday Night Group MTB Ride at Evergreen Park

    Evergreen Park, Sheboygan, WI 53083, United States, Sheboygan · verified Sep 13
    See details

    Hit the trails at Evergreen Park and Quarry Park for a Tuesday night group mountain bike ride hosted by SCC. These rides run from June through October and typically offer two options when turnout allows, a fast group for experienced riders and a chill no-drop group. Meet in the Quarry Park parking lot. This outing takes place at dusk, so lights are recommended. After the ride, snacks are provided by SCC, and it is BYOB. Organizers use a Facebook event for each ride to share weather and trail updates and to plan for snacks. All ages are welcome, with riders under 18 required to be accompanied by an adult. Helmets are required for everyone, a mountain bike is needed for MTB trails, and participation is at your own risk.

    Event website ↗
  • 6pm

    Cooking Class: Cooking Under Pressure

    Relish, 811 N 8th St, Sheboygan · verified Sep 13
    See details

    At Relish, instructor Maryjo Evenson leads a demonstration that highlights how electric pressure cookers can trim cooking time by up to 70 percent and support healthy meals. Whether you use an Instant Pot, a Fagor, or another model, see how this multipurpose tool can handle pressure cooking, slow cooking, rice, and yogurt in one compact machine. Maryjo shares practical tips and techniques while preparing a lineup of comfort favorites, including Italian beef, risotto, and creamy mac and cheese. This is a demonstration-style class. Cost is $49.

    Event website ↗
Wednesday, September 23 3 events
  • 8am

    Scio Sheboygan Summer Farmers Market

    Fountain Park , 834 Ontario Ave, Sheboygan · verified Sep 15
    Free

    Explore the SCIO Sheboygan Summer Farmers Market at historic Fountain Park, where local growers and makers share the flavors of Wisconsin. Shop for just-picked produce, local meats, eggs, cheese, and fresh-baked treats, and browse colorful flowers, food truck fare, and handmade crafts from vendors located within 100 miles. FoodShare and EBT are accepted at the SCIO Information Booth, with Double Your Bucks matching available up to $20 per day on fresh fruits and vegetables. WIC and SFMNP vouchers are also welcomed. Prospective vendors are invited to apply to participate.

    Event website ↗
  • 9am

    Homeschool Days

    Wade House , Glenbeulah · verified Sep 15
    See details

    Homeschool and other non-traditional learners can explore the horse-powered past of Wisconsin at Wade House. Step into a reproduction stagecoach to learn about plank road travel, try hands-on model carriage building in the Wesley W. Jung Carriage Museum, then ride a horse-drawn wagon over the Mullet River to the historic area where costumed interpreters demonstrate blacksmithing and sawing using muscle and water power. The experience includes a tour of the 27-room Stagecoach Hotel that once welcomed travelers along the plank road. Programs take place both outdoors and inside museum buildings, rain or shine, so dressing for the weather is recommended. Plan for a visit that may last up to four hours. Guests may bring their own lunch, with lunch space available upon request. Admission is 6 dollars for students in grades K through 12, 3 dollars for preschoolers, and free for infants and toddlers. Adults ages 18 to 64 are 11 dollars and seniors 65 and older are 11 dollars. Adult chaperones require a ticket at 11 dollars each. Advance registration is required. Society members receive a 10 percent discount with membership verification at checkout.

    Event website ↗
  • 7pm

    Sheboygan, WI @ the Limelight Pub

    Limelight Pub, 1702 S 17th St, Sheboygan · verified Sep 13
    See details

    At Limelight Pub in Sheboygan, Jack Yoder takes the stage with The Doublewide Disaster for a night of Americana steeped in blues grit and alt-country, with vivid stories set to driving, toe-tapping grooves. Based in Denver, Yoder is a singer and songwriter with more than three decades of experience as a solo artist and as a sideman in rockabilly, cowpunk, rock, and outlaw country, bringing a mix of seasoned craft and lively spontaneity. He is joined by Tony Hecker on drums and Joe Colomb on bass, and together the trio turns his songs into a full-bodied live sound with honky-tonk edge and a warm, soulful feel. Their single Drunken Lament captures the band’s character, while Dumpster Fire showcases gritty narratives and propulsive rhythms through tracks like I Made It to Here, Hammer Down, and the more vulnerable I’ll Still Be Your Friend. Earlier releases such as Wagonload and the Southern Crescent 4-Track EP blend originals with a cover of R.E.M.’s Driver 8. The performance is rooted in blues, country, and rock traditions, shifting from high-energy anthems to quiet ballads that keep the storytelling at the heart of the music.

    Event website ↗

All upcoming events91 more events through Dec 5

Everything else on Plymouth's calendar over the next 30 days, in order.

Thursday, September 24 2 events
  • 5pm

    Harvest Moon Pop Up

    Restoration Orchards & Market , Sheboygan Falls · verified Sep 15
    See details

    Celebrate the harvest season with an evening at the orchard featuring food, local vendors, and live music. Harvest Street Food Truck will serve a menu of savory bites, joined by additional vendors sharing samples and treats. Jamie Odekirk provides the soundtrack for a relaxed night as guests stroll the grounds. Heirloom apples are in season, and, if available, the popular apple cider may make an appearance. Families can wander, listen, sample, and grab dinner while taking in the sights and sounds of the harvest. Admission is free, the event is outdoors, and it welcomes all ages.

    Event website ↗
  • 6pm

    Open Jam Thursdays

    Rumors Roadhouse, Plymouth · verified Sep 15
    See details

    Enjoy an open jam where musicians at every experience level are welcome to make music together. On-site gear includes a bass guitar with amps, a keyboard, an accordion, and a drum kit, making it easy to jump in and play alongside others.

    Event website ↗
Friday, September 25 7 events
  • 10am

    Farmers Market

    LaValley Home & Garden, 820 Madison Ave, Sheboygan · verified Sep 13
    Free

    The Farmers Market at LaValley brings together a curated group of local growers and makers to create a distinctive, quality-focused marketplace. Explore goods from area vendors, connect with the people behind their craft, and enjoy a welcoming setting at LaValley Home and Garden that showcases local talent and community spirit.

    Event website ↗
  • 4pm

    SoLu Estate's Farmer's Market & Craft Fair

    SoLu Estate Winery, Cascade · verified Sep 15
    Free

    SoLu Estate brings together local farmers, crafters, artists, and more for a farmer’s market and craft fair set up in the parking lot. Admission is free. Shoppers can explore a wide range of handmade goods and specialty items, then unwind on the patio with a glass of wine while enjoying free live music. Participating vendors include Beige Boutique, Blonde Russian Boutique, Bloomin on Broadway, Bodden's Bees LLC, Brynn Taylor Designs, Cady’s Crochet Corner, Cafe Floriana, CJL Threads, Der Hoffskeller, Hand Made by Nancy Brown, Homemade Pickles, Infernal Candles (DBA Infernal Fragrances), Joe & Linda's Soft Cashew Brittle, JV Sourdough Creations, La Belle Vie, Lefty Jean’s Creations, L'BRI, Mary Kay, Moonlit Grove, Ollie Skincare, Poppy Fills Bobo Balloon Arrangements, Sealed with a Spark LLC, Shampoo Sense by Sydney, Shrush Design, The Happy Harvest, and The Lucky Sock Shop.

    Event website ↗
  • 5:30pm

    Random Lake Color Run

    School District of Random Lake track , Random Lake · verified Sep 15
    See details

    The 9th annual Color Run brings a family friendly two mile run or walk to the School District of Random Lake. Sponsored by Jolly Good and organized by Friends of Random Lake Kids, this community event mixes colorful fun with an easygoing course suitable for all ages. After the finish, participants can enjoy Jolly Good, treats from food trucks, and a glow party.

    Event website ↗
  • 5:30pm

    Beef Wellington

    The Osthoff Resort & Spa, 101 Osthoff Ave, Elkhart Lake · verified Sep 13
    See details

    Enjoy a hands-on cooking class focused on a traditional lineup of dishes. With a chef leading the way, participants prepare Beef Wellington, mushroom duxelles, Bordelaise sauce, mashed potatoes, and haricot verts while practicing core techniques in an inviting setting. Each attendee receives two complimentary beverages. The cost is $99 per person, plus tax and fees, and tickets are nonrefundable.

    Event website ↗
  • 5:30pm

    All Ages Bike Rides

    St. Luke United Methodist Church, 623 Ontario Ave, Sheboygan · verified Sep 13
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    Participants gather at St Luke for a fun, all-ages bike ride. Bring a bike, a helmet, and a water bottle, and get ready to enjoy time on two wheels.

    Event website ↗
  • 7pm

    Getting you shaking your groove thing

    Rumors Roadhouse, Plymouth · verified Sep 13
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    Rumors Roadhouse hosts a laid-back outing with smoked meats and cold beer, paired with a lively vibe that gets people moving. Expect hearty flavors, refreshing drinks, and an upbeat atmosphere made for cutting loose.

    Event website ↗
  • 7pm

    Swift Nation – The Ultimate Taylor Swift Tribute Show

    Weill Center for the Performing Arts, 826 N 8th St, Sheboygan · verified Sep 13
    See details

    Experience a high-energy, family-friendly tribute concert celebrating the music and eras of Taylor Swift, presented by the Plymouth Advancement Association and sponsored by Masters Gallery Foods. Founded and produced by David Yuter, this production aims to capture the spirit, sound, and excitement of the Eras Tour with care and accuracy. The show is led by vocalist Star Melody Ebner, whose career spans dozens of bands across San Diego, guiding the audience through an unforgettable sing-along. Since launching in 2024, the production has played more than 100 shows across over 30 U.S. states, reaching hundreds of thousands of fans and setting attendance records. Highlights include appearances at Mohegan Sun Arena and the Pacific Amphitheatre, with an international expansion planned for Asia, Dubai, and Australia. Expect elite musicians, professional dancers, faithful choreography, era-spanning costumes, and original arrangements that bring Taylor’s catalog to life with pop flair and rock-show energy. The atmosphere welcomes multiple generations, creating a positive, community-centered experience for parents, kids, and friends. Tickets are priced from $35 to $79. Doors open one hour before showtime. All sales are final, with no refunds, exchanges, or weather cancellations. Official ticketing is handled through TicketSearch, and there is no affiliation with secondary ticket marketplaces. This tribute act performs the songs of Taylor Swift in an unofficial capacity and is not endorsed by or affiliated with Taylor Swift, TAS Rights Management, or their related entities. More information will be shared as it becomes available.

    Event website ↗
Saturday, September 26 14 events
  • 8am

    SCIO Sheboygan Summer Market

    Fountain Park , Sheboygan · verified Sep 15
    Free

    The SCIO Sheboygan Summer Farmers Market fills the historic Fountain Park with the flavors and creativity of local producers. Explore in-season fruits and vegetables, locally raised meats, farm eggs, cheese, baked treats, cut flowers, meals from food trucks, and handcrafted goods from vendors located within 100 miles. FoodShare and EBT are accepted at the SCIO information booth, and the Double Your Bucks program offers a daily match up to $20 on fresh fruits and vegetables. WIC and SFMNP vouchers are also welcomed.

    Event website ↗
  • 9am

    Fallooza Fall Festival & Music

    Plymouth City Park, 203 Suhrke Rd, Plymouth · verified Sep 13
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    Celebrate the fifth year of Fallooza at Plymouth City Park with a full day of music and festival fun that supports addiction and mental health services in Sheboygan County. Since 2022, the event has generated more than $375,000 to benefit Mental Health America Lakeshore, Rogers Behavioral Health Sheboygan, Samaritan's Hand, and Pathways to a Better Life Kiel. Enjoy live performances, distinctive vendors, face painting, bounce houses, and other activities. Additional surprises are planned.

    Event website ↗
  • 9am

    Teen Driving Program

    Road America, Plymouth · verified Sep 13
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    At the Road America Teen Driving Program, young drivers receive hands-on instruction that goes beyond standard driver education. In a controlled, off-street environment that prioritizes safety, this course recognized nationwide places participants in simulated real-world situations to strengthen decision making and vehicle control. Teens practice key defensive techniques, including emergency braking, recognizing hazards, and avoiding collisions, to promote confidence, responsibility, and safer driving habits. Parents are welcome to attend alongside their teens.

    Event website ↗
  • 9am

    Blacksmithing Workshops

    Wade House , Glenbeulah · verified Sep 15
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    Learn traditional blacksmithing inside the 1860s Dockstader Blacksmith Shop at Wade House. This half-day workshop focuses on creating a single knife from start to finish. With guidance from a skilled blacksmith, you will heat steel in the forge, hammer it to shape, and finish it with a personalized handle to take home a one-of-a-kind piece. Participants must be at least 13 years old. Expect sustained work at the anvil and forge around high heat. Wear sturdy closed-toe shoes or boots, secure long hair, avoid loose clothing, and choose clothing that can get dirty. Gloves and safety glasses are provided. Bringing a water bottle is recommended. Advanced registration is required. The fee for the half-day session is $125 per person, and society members receive a 10 percent discount with membership verification at checkout. The program runs rain or shine. Off-street parking is available. Restrooms are in a nearby building within walking distance. Service animals are permitted, pets are not. The blacksmith shop is wheelchair accessible, though the terrain is uneven and the activity involves standing for long periods and tolerating heat. Wade House is a historic site featuring a restored stagecoach inn, a working blacksmith shop, a sawmill, and the Wesley W. Jung Carriage Museum, offering a setting that reflects Wisconsin’s horse-powered past.

    Event website ↗
  • 10am

    Gemstone Sluice Mining

    M&T's Gibbsville, Sheboygan Falls · verified Sep 15
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    Returning for the Annual Harvest Festival, The Tinker Shoppe from Mayville, Wisconsin brings a hands-on gemstone sluice where participants wash dirt to uncover real stones and keep every treasure they discover. The activity is suitable for all ages and offers a simple way to experience old-time mining. Their booth also features a selection of board games, toys, gemstones, and items made from stone.

    Event website ↗
  • 10am

    Community Market

    Margo's, 118 N 9th St, Oostburg · verified Sep 13
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    A community-run market in the heart of Oostburg, Wisconsin, created by and for local residents. It takes place on the second and fourth Saturdays in June, July, August, and September. Vendors interested in participating can email shopatmargos@gmail.com to reserve a spot or ask questions.

    Event website ↗
  • 11am

    Mortal Matters: A Death and Dying Bookclub

    WordHaven BookHouse, 923 N 8th St, Sheboygan · verified Sep 15
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    At WordHaven BookHouse, LLC, Mortal Matters brings people together to read and talk about death, dying, grief, and the wider human experience. Participants cultivate a considerate space for curiosity, reflection, and open conversation around topics that are often unspoken. Books are selected and shared ahead of time, so you can take part when a title or theme resonates, whether attending regularly or choosing the discussions that speak to you. The gathering welcomes everyone and requires no professional background or prior experience, only a willingness to listen, reflect, and engage with respect. This is a discussion-focused group for learning and connection, not a grief support or counseling program.

    Event website ↗
  • 12pm

    Nitro Five

    M&T's Gibbsville, Sheboygan Falls · verified Sep 15
    Free

    NITRO FIVE, a five-piece rock cover band from Sheboygan, performs at M&T's Gibbsville Orchard with energetic covers of Journey, AC/DC, Cheap Trick, and Blink-182. The setting includes apple picking, a gift and bakery shop, and outdoor games. Food and beverages are available for purchase. Pets and carry-ins are not permitted, and admission is free.

    Event website ↗
  • 1pm

    Bingo Pub Crawl Launch Party

    Falls Tap, 212 Pine St, Sheboygan Falls · verified Sep 13
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    At Falls Tap, the celebration begins with the monthly meat raffle held in support of Falls Tap and Paws Up Pet Rescue, then continues with music and karaoke. 50/50 and bucket raffles run throughout the event, and there will be information about the upcoming Bingo Pub Crawl presented by 12-Days of Christmas. Drinks and food from Falls Tap are available to enjoy while taking part. The focus is on community support and learning more about the missions of 12-Days of Christmas and Paws Up Pet Rescue.

    Event website ↗
  • 2pm

    Sheboygan and Surrounding Counties Mini Golf & Down Syndrome Awareness Walk 2026

    Harbor Pointe Mini Golf, 322 S Pier Dr, Sheboygan · verified Sep 13
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    Registration is open for the DSAW-Sheboygan Mini Golf and Down Syndrome Awareness Walk at Harbor Pointe Mini Golf. This community gathering features mini golf, face painting, crafts, and balloon art, the 21 Showcase Red Carpet Celebration, a scenic walk along the Sheboygan harbor, and raffles, snacks, and other family-friendly activities. The event brings people together to celebrate achievements, raise awareness, and support individuals with Down syndrome and their families throughout the region. Funds raised help DSAW provide programs, resources, advocacy, and support to more than 5,500 individuals with Down syndrome and their families across Wisconsin.

    Event website ↗
  • 2:30pm

    Pottery Class

    MAS Arts Studio, 811 New York Ave, Sheboygan · verified Sep 13
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    Discover the pottery wheel in a welcoming class at MAS Arts Studio. Designed for beginners, this hands-on session teaches foundational techniques, encourages creativity, and guides participants to finish a handmade piece to take home. Multiple session times are available.

    Event website ↗
  • 4:30pm

    Beef Wellington

    The Osthoff Resort Cooking School, 101 Osthoff Ave, Elkhart Lake · verified Sep 13
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    Explore classic technique in a cooking school class centered on Beef Wellington. Prepare the full plate, including mushroom duxelles, Bordelaise sauce, mashed potatoes, and haricot verts, with step-by-step guidance from the chef and practical techniques shared in a welcoming environment. Each participant receives two complimentary beverages. The price is $99 per person, plus tax and fees, and tickets are non-refundable.

    Event website ↗
  • 4:30pm

    Sunset Cruise

    Road America, Plymouth · verified Sep 15
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    Drive your own vehicle on America’s National Park of Speed during a relaxed sunset experience. This low-speed outing features three picturesque laps around Road America’s celebrated four-mile course as golden light settles over the track. It welcomes car enthusiasts, families, and anyone who wants time on the circuit without competition, offering space to absorb the sounds, scenery, and atmosphere of a legendary racing destination. Available on select dates from May through September. Capacity is limited, so advance registration is required.

    Event website ↗
  • 9pm

    Karaoke

    Mikes Kiel Lounge, 212 Fremont St, Kiel · verified Sep 13
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    On the second and fourth Saturdays of each month, Mike's Kiel Lounge features a night of karaoke paired with music trivia. It offers a blend of singing and music know-how in one gathering.

    Event website ↗
Sunday, September 27 4 events
  • 12pm

    Myles Wangerin

    M&T's Gibbsville Orchard, Sheboygan Falls · verified Sep 13
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    Myles Wangerin returns to M&T's Gibbsville Orchard after a couple of years for a live solo performance. The WAMI Award recipient and singer songwriter brings guitar driven music influenced by Garth Brooks, Brad Paisley, The Steve Miller Band, and AC/DC. Beyond the music, the orchard offers games, apple picking, a bounce house, a gift store, and more. Food and beverages are available for purchase, carry ins are not allowed, pets are not permitted, and there is no cover charge. Seating is limited, so bringing lawn chairs is recommended.

    Event website ↗
  • 2pm

    Arts at the Waelderhaus- Built with Purpose: The History of the Village of Kohler

    Waelderhaus, 1100 W Riverside Dr, Kohler · verified Sep 13
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    Explore how one of the nation’s most intentionally designed communities took shape. A program with local photographer Darryl Gumm traces the Village of Kohler’s beginnings and its growth alongside the Kohler Company, highlighting the people and ideas that shaped its distinct character. With an emphasis on forward-looking design and an enduring focus on quality of life, it illuminates the history and heritage that still shape Kohler today.

    Event website ↗
  • 3pm

    The Foocoustics

    Edgewater Bar & Grill, 820 State Road 67, Kiel · verified Sep 13
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    The Foocoustics take the stage at Edgewater Bar and Grill with a set packed with 90s and 2000s favorites along with a few timeless classics. Expect songs by Green Day, Foo Fighters, Nirvana, STP, Pearl Jam, Tom Petty, Modest Mouse, The Killers, Blink 182, Bryan Adams, Chris Cornell, Creed, Fall Out Boy, Gin Blossoms, Goo Goo Dolls, Third Eye Blind, Sublime, Oasis, Matchbox 20, The Smashing Pumpkins, Talking Heads, Pink Floyd, The Proclaimers, Radiohead, and Jane's Addiction.

    Event website ↗
  • 6:30pm

    Moonlight Paddle

    Downtown Sheboygan, 2202 Indiana Ave, Sheboygan · verified Sep 15
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    Silent Wake brings its annual full moon paddle series to Downtown Sheboygan, Wisconsin, offering a chance to paddle the Sheboygan River by moonlight. Night kayaking provides a new perspective, and the route is chosen for minimal boat traffic to help ensure a safe experience. The pace is relaxed and the group stays together. This outing is recommended for participants with prior paddling experience. The cost is $45 per person per outing, with a limited group size of 8 that often fills quickly. Before launching, participants receive kayaks, gear, and white lights, with help provided for proper fitting. Those bringing their own kayak and equipment may do so at the same price and should have everything unloaded and ready before launch. A safety talk takes place on shore, lights remain on while on the water, and everyone follows the lead safety boater. If weather requires adjustments, notice will be provided.

    Event website ↗
Thursday, October 1 1 event
  • 9am

    Sheboygan October Meetup: Caffeine & Cashflow | Networking for Full-Time Investors

    Field to Fork, 505 S 8th St, Sheboygan · verified Sep 13
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    Wisconsin’s largest real estate investor networking event brings Caffeine & Cashflow to Sheboygan for a morning focused on networking and growth. The format has no pitch, no agenda, and no sponsors. The focus is 100 percent networking for business owners, real estate investors, entrepreneurs, and other high performers who value growth through collaboration. Attendees are encouraged to arrive with an open mind and be ready to share what they are working on, what they are best at, and something they could use help with in their business. The community embraces competition through collaboration, with ambitious people challenging each other to grow. Free parking is available in the back. The meetup gathers between Field to Fork and Il Ritrovo in the bar area, where the connected buildings meet. Regular gatherings are hosted in Sheboygan, with additional monthly meetups in Green Bay, Appleton, La Crosse, Delafield, Milwaukee, and Watertown.

    Event website ↗
Saturday, October 3 6 events
  • 10:30am

    Brace's Smoke Pit BBQ

    M&T's Gibbsville , Sheboygan Falls · verified Sep 15
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    Brace's Smoke Pit BBQ brings wood-fired, low and slow barbecue from Dodge County to M&T's Gibbsville Orchard. The food trailer will be on site alongside family-friendly activities that include an 18-hole mini golf course, live music, outdoor games, and apple picking. Come hungry and make a day of it.

    Event website ↗
  • 11:30am

    Moon Pool Band

    M&T's Gibbsville, Sheboygan Falls · verified Sep 15
    Free

    Moon Pool makes its debut at M&T's Gibbsville Orchard, bringing a set of familiar songs delivered with real skill and a youthful spark. The young band earned a top 10 finish in 2025 at Summerfest's Battle of the Bands. In addition to the live music, families can enjoy 18 holes of mini golf, a food truck, outdoor games, tractor wagon rides, apple picking, and more. Event guidelines include no pets, no carry-ins, and no cover charge.

    Event website ↗
  • 11:45am

    TRY HOCKEY FOR FREE

    Sheboygan Lakers Ice Center, 1298 S Wildwood Ave, Sheboygan · verified Sep 13
    Free

    Hosted by the Sheboygan Lakers at the Sheboygan Lakers Ice Center, this free introduction to hockey welcomes boys and girls to get on the ice, learn the basics, and have fun exploring the sport. No prior experience is required, and all skill levels are welcome. Tie your skates, take a few shots, and see what makes hockey exciting.

    Event website ↗
  • 1pm

    Wade House Hikes

    Wade House, Glenbeulah · verified Sep 15
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    Explore the Wade House Historic Site on a guided hike into the Kettle Moraine with naturalist Jim Willaert. Walk through rolling countryside, hardwood forests, meadows, streams, and quiet glades surrounding the historic Stagecoach Inn while discovering how and why leaves shift to vibrant shades in autumn. This seasonal series highlights different facets of the grounds throughout the year, and this edition invites a closer look at local flora and fauna as the landscape changes. Wear sturdy hiking footwear and dress for the weather. Bring water only. Restrooms and water fountains are available on site. Pets are not allowed, though service animals are welcome. Guests with additional mobility needs are encouraged to contact the site in advance. Advanced registration is required. Admission is $6 for adults and teens, $5 for seniors, $3 for children ages 5 to 11, and free for children under 5. Society members receive a 10 percent discount with verified membership.

    Event website ↗
  • 7pm

    Karaoke

    Conrad’s 2nd Knot, 19133 County Road XX, Kiel · verified Sep 13
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    Conrad's 2nd Knot hosts a recurring karaoke gathering that offers a simple way to step away from day-to-day life. Expect a welcoming, lively atmosphere and food available while participants enjoy karaoke together.

    Event website ↗
  • 7pm

    John McGivern: A Man for All Seasons

    Weill Center for the Performing Arts, 826 N 8th St, Sheboygan · verified Sep 13
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    John McGivern returns with A Man for All Seasons, a storytelling performance that finds humor in both the turning of the calendar and the passages of life. He moves from spring’s fresh beginnings and eager anticipation, to summer’s bright long days and quick growth, to autumn’s warm-toned moments that become lasting memories, then to winter’s reflective quiet with pale whites and long, cold nights, all tied together with steady laughter. Presented by the Optimist Club of Sheboygan and sponsored by Bank First. Reserved seating is available in four tiers. Tier 1 is $60 plus fees. Tier 2 is $55 plus fees. Tier 3 is $45 plus fees. Tier 4 is $35 plus fees. Doors open one hour before the performance. All sales are final with no refunds, exchanges, or weather-related cancellations. Ticketing is handled by the Weill Center through TicketSearch, and secondary ticket marketplaces are not affiliated.

    Event website ↗
Sunday, October 4 1 event
  • 12pm

    The Stewed Tomatoes

    M&T's Gibbsville, Sheboygan Falls · verified Sep 15
    Free

    M&T's Gibbsville Orchard features food and beverages, mini 18 hole golf, outdoor games, and apple picking. Onstage, The Stewed Tomatoes make their first appearance at the orchard with an acoustic set that blends country, pop, rock, and blues with their own twist to keep the energy up. Event guidelines include no pets and no carry-ins. There is no cover charge.

    Event website ↗
Monday, October 5 1 event
  • 6pm

    Queer Fam Game Night

    Paradigm Coffee and Music, 1202 N 8th St, Sheboygan · verified Sep 13
    Free

    Queer Fam Game Night brings a relaxed evening of tabletop fun to Paradigm Coffee and Music. The gathering is free and welcomes the LGBTQ+ community and allies. Multiple tables will be available so everyone can choose which games to jump into. Bring favorite games from home or play from the many provided on site. To keep cards and boards clean, please skip Cheetos so no one leaves with orange fingerprints. This event is part of the 2026 Queer Fam Game Nights series.

    Event website ↗
Wednesday, October 7 1 event
  • 6:30am

    An Evening With Al and Lisa Robertson

    New Life Community Church, 2323 Eastern Ave, Plymouth · verified Sep 13
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    Enjoy an evening with Al and Lisa Robertson, known from Duck Dynasty and the Unashamed podcast, as they share the real story of their marriage, including the highs, the difficult seasons, and how grace, forgiveness, and redemption reshaped their relationship. The program features their testimony along with a live Q&A, offering encouragement that any story can be redeemed. This event welcomes married couples, engaged pairs, singles, and anyone seeking a night of inspiration. Childcare is available. Registration is required and free.

    Event website ↗
Thursday, October 8 4 events
  • 7am

    Track Day

    N7390 Wi-67, Plymouth, WI, United States, Wisconsin 53073, Plymouth · verified Sep 13
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    Take to a premier North American road course in your own high-performance or track-prepared car, all in a non-competitive track day format. Available groups are Novice at $425, Intermediate at $395, and Advanced at $395. Vehicles must be suited to non-competitive track day use.

    Event website ↗
  • 4:30pm

    Game Night

    Plymouth Public Library, 130 Division St, Plymouth · verified Sep 13
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    Spend an evening at the library enjoying board games with family, friends, and neighbors. Choose from classic favorites or explore new titles, with all games supplied on site. Children under 10 must attend with a caregiver.

    Event website ↗
  • 4:30pm

    Shipbuilders Soccer @ Sheboygan North

    Horace Mann Soccer Fields, 2820 Union Ave, Sheboygan · verified Sep 13
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    The Shipbuilders face Sheboygan North in a WIAA FRCC soccer matchup at Horace Mann Soccer Fields. The schedule features a JV1 game followed by the varsity match.

    Event website ↗
  • 7:30pm

    Karaoke

    Hika Bay Tavern, 252 Lincoln Ave, Cleveland · verified Sep 13
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    Karaoke at Hika Bay Tavern comes with a twist, adding music trivia to the mix. While enjoying the entertainment, guests can take advantage of the tavern’s daily specials and pizza.

    Event website ↗
Friday, October 9 1 event
  • 3pm

    Live Music with Anna Marie

    Flora Fields, 122 Grafton Ct, Kohler · verified Sep 15
    See details

    Flora Fields will feature live music. Additional details, including performer information and event updates, will be shared as they become available.

    Event website ↗
Saturday, October 10 6 events
  • 8am

    2026 Charity Ride

    Sauk Trail Conservation Club, Cedar Grove · verified Sep 13
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    Attendees can explore the local area on guided ATV and UTV rides, then enjoy dinner, raffles, and an online auction. The event takes place at Sauk Trail Conservation Club. More details will be shared soon.

    Event website ↗
  • 9:30am

    Autumn Celebration Weekend

    Wade House, Glenbeulah · verified Sep 15
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    Celebrate the season at Wade House Historic Site with hands-on autumn traditions for all ages. Carve pumpkins, press apples, and try classic games like Snap Apple. Visit the candlelit Herrling Sawmill to hear the rhythmic churn of an up-and-down water-powered saw and enjoy family-friendly spooky stories from the past. Warm up with hot apple cider and take a horse-drawn carriage ride across the grounds. The Stagecoach Inn, Dockstader Blacksmith Shop, Herrling Sawmill, and the Wesley W. Jung Carriage Museum are open to explore. A featured talk by author and heirloom apple scholar Dan Bussey highlights Wisconsin apple varieties and the influence of Native communities and immigrant families on what was grown. Tickets are $17 for adults ages 18 to 64 and $17 for teens ages 13 to 17, $15 for seniors 65 and older, $8.50 for children ages 5 to 12, and free for children under 5. Society members receive a 10 percent discount. The site is open rain or shine. Guests may exit and return throughout the day. Restrooms and water fountains are available, and only water may be brought in from outside. Comfortable walking shoes and weather-appropriate clothing are recommended. Pets are not permitted, with the exception of service animals. Carriage rides may not accommodate all mobility needs, and because of the historic nature of the buildings, not all areas are ADA accessible. For accessibility questions, contact 920-526-3271 or wadehouse@wisconsinhistory.org. The museum store is open during business hours. For general questions, contact 608-264-4848 or boxoffice@wisconsinhistory.org. Wade House Stagecoach Inn once welcomed travelers along the busy route between Fond du Lac and Sheboygan. The 27-room Greek Revival hotel operated until about 1872, was restored beginning in 1950 by the Kohler family and Kohler Foundation, became part of the Wisconsin Historical Society, and opened to the public in 1953. Today the site includes the historic inn, a blacksmith shop, a working sawmill, and the Wesley W. Jung Carriage Museum, home to Wisconsin’s largest collection of carriages and wagons. Horse-drawn rides connect the visitor center with the historic core.

    Event website ↗
  • 10am

    Off Road Driving Experience

    N7390 Wi-67, Plymouth, WI, United States, Wisconsin 53073, Plymouth · verified Sep 13
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    Take on wooded off-road trails across Road America’s 640-acre property during a UTV ride lasting more than two hours. Participants operate Yamaha Wolverine RMAX Series and Yamaha Viking side-by-sides over varied terrain featuring hills, large rocks, logs, and, weather permitting, mud. Pricing is $120 per person for double occupancy. This experience runs rain or shine, and bringing extra clothing is recommended in case of inclement weather.

    Event website ↗
  • 11:30am

    The Cheese Doodles

    M&T's Gibbsville Orchard, Sheboygan Falls · verified Sep 13
    Free

    Enjoy a lively set from The Cheese Doodles at M&T's Gibbsville Orchard. The duo spans many musical styles and welcomes song requests if there is a tune you want to dance to. Families can pick apples, try pumpkin smashing, and take pony rides, with food and drinks available at the pavilion. Please note that pets and carry ins are not permitted. There is no cover charge.

    Event website ↗
  • 1pm

    Community Art Critique

    Ampersand Supply Co, 1212 N 8th St, Sheboygan · verified Sep 13
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    A friendly, relaxed critique session where everyone has a voice. Participants may bring artwork to present, or arrive ready to observe carefully and offer thoughtful feedback to others. The purpose extends beyond receiving notes, aiming to sharpen the eye, strengthen the voice, and nurture a sense of creative community. Conversation touches on composition, concept, technique, and intention, approached with honesty, curiosity, and respect. Works in progress and completed pieces are equally welcome, and every viewpoint matters. Come with a piece to share and the ideas behind it, and know that your perspective might be exactly the encouragement another creator needs.

    Event website ↗
  • 7pm

    John Gay Returns

    Rumors Roadhouse, Plymouth · verified Sep 15
    See details

    Enjoy live music from a talented performer alongside smoked meats and adult beverages.

    Event website ↗
Sunday, October 11 3 events
  • 11am

    Bavarian Apfelfest

    Restoration Orchards & Market , Sheboygan Falls · verified Sep 15
    See details

    Apfelfest, the German apple festival, celebrates the fall harvest with an array of apple flavors and traditions. The event features apple-focused desserts, drinks, and treats, including apfelkuchen, cider donuts, and hot apple cider, along with fresh apples, pre-picked selections, and heirloom, artisanal apple ciders. Bavarian foods, the Harvest Street Food Truck, German music, and a variety of vendors round out the festivities and highlight the season’s bounty.

    Event website ↗
  • 12pm

    Mark Wayne

    M&T's Gibbsville Orchard, Sheboygan Falls · verified Sep 13
    See details

    Entertainer, producer, and steel guitarist Mark Wayne delivers a mix of gospel and country in the spirit of Randy Travis, Johnny Cash, Ricky Skaggs, and others at M&T's Gibbsville Orchard. Activities include apple picking, tractor wagon rides, a petting zoo, and a gift store filled with fall favorites like apple pies and apple cider. Pets are not allowed and carry ins are not permitted.

    Event website ↗
  • 4:30pm

    Karting Experience - Practice, Qualify, Race

    Road America, Plymouth · verified Sep 15
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    Take the wheel at the Briggs & Stratton Motorplex at Road America for a three-part karting experience that combines practice, qualifying, and a race. Tackle a technical course packed with corners and reach speeds up to 40 mph in karts supplied on site. Each on-track segment runs about 10 minutes to build confidence and pace. Participants should arrive 15 minutes before the scheduled start. Closed-toe shoes and long pants are required. Full-face helmets are provided, or bring your own if preferred. Drivers must be at least 14 years old, and those under 18 need a parent or guardian present. A drivers meeting is mandatory at the start. Spectator passes will be available for purchase on the day of the event for $5.

    Event website ↗
Friday, October 16 1 event
  • 7am

    Track Day

    N7390 Wi-67, Plymouth, WI, United States, Wisconsin 53073, Plymouth · verified Sep 13
    See details

    Drive your own high-performance or track-prepared vehicle, suitable for non-competitive track day use, on one of North America’s premier road courses. Options are available for every experience level, with pricing at $425 for Novice and $395 for both Intermediate and Advanced.

    Event website ↗
Saturday, October 17 5 events
  • 9:30am

    Stagecoach Saturdays

    Wade House, Glenbeulah · verified Sep 15
    See details

    Take a leisurely 30-minute ride through the scenic Kettle Moraine in a faithful Concord stagecoach replica. Guests can meet the horses, take photos, and learn about late 1800s travel by horsepower. The coach comfortably seats six passengers per tour, and larger parties may be accommodated with advance coordination. Continue the day with tickets that include the broader Wade House Historic Site, featuring the 27-room Greek Revival Stagecoach Inn, a sawmill, a blacksmith shop, and the Wesley W. Jung Carriage Museum, home to Wisconsin’s largest collection of carriages and wagons. Admission is $15 for adults ages 18 to 64 and for teens ages 13 to 17, $13 for seniors 65 and older, $10 for children ages 5 to 12, and $3 for children under 5. Society members receive a 10 percent discount with verified membership. Advance registration is recommended, with same-day rides offered as space allows. Check-in takes place at the Wade House Visitor Center and Wesley W. Jung Carriage Museum, and all participants must be present for a brief safety talk before boarding. For the safety of guests and staff, rides may be canceled and fully refunded if severe weather is expected.

    Event website ↗
  • 11am

    JUNIOR'S EATS FOODTRUCK

    M&T's Gibbsville Orchard, Sheboygan Falls · verified Sep 13
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    Junior's Eats food truck returns to M&T's Gibbsville Orchard for a day of great food, live music, apple picking, and the search for the perfect Halloween pumpkin. Families can enjoy outdoor games, tractor wagon rides, and a bounce house, along with more activities. No carry-ins are allowed.

    Event website ↗
  • 11:30am

    Andy Braun Music

    M&T's Gibbsville Orchard, 3322 WI-32, Sheboygan Falls · verified Sep 13
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    Spend a crisp fall outing at M&T’s Gibbsville Orchard picking apples, searching for the perfect pumpkin, and enjoying bites from Junior Eats FoodTruck while Andy Braun performs live. This singer songwriter brings acoustic guitar, vocals, and harmonica together for a folk rock sound influenced by Neil Young, Van Zandt, Tom Petty, and Johnny Cash. Guests are welcome to bring a lawn chair for comfort, but carry-ins are not allowed.

    Event website ↗
  • 12pm

    Live Music with Anna Marie at Flora Fields in Kohler, WI

    Flora Fields, 122 Grafton Ct, Kohler · verified Sep 15
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    Flora Fields is set to host a live music performance. Additional details will be shared as they become available.

    Event website ↗
  • 7pm

    Lindsay and Jon Return

    Rumors Roadhouse, Plymouth · verified Sep 13
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    BBQ and beverages pair with live music from Lindsay and her partner Jon. Originally from Waukesha, Wisconsin, Lindsay delivers acoustic covers that span multiple genres. She is sometimes nicknamed Joanie Cash for her frequent tributes to Johnny Cash.

    Event website ↗
Sunday, October 18 2 events
  • 8am

    Road America AutoCross Series 10/18/2026

    Road America, Plymouth · verified Sep 13
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    Experience timed competition at the Briggs & Stratton Motorplex as drivers chase the quickest runs on a course that changes each round. Backed by FVSCC, results count toward season points and the series crowns its own champion. Championship scoring uses your best four events, with up to two drops if you compete in all five, and one round is a double-header spanning Turn 14 Paddock and the Motorplex. Prizes for the champion include entry to a Winter Autocross Series, a weekend pass for two to a Road America public race weekend, and championship hardware. SCCA classes and autocross rules apply. A DOT-approved helmet is required and every car must pass a basic safety inspection. The day features check-in at Gate 4, time to walk the course, a drivers meeting, competition runs, and awards. Driver entry is $75 and includes admission for two spectators who arrive with the driver at entry. Spectator admission is $10, and children 16 and under are free. Food will be available for purchase from onsite concessions. The field is limited to 150 drivers, and live timing will be available.

    Event website ↗
  • 1pm

    Forest Floor with Mel Kolstad

    Ampersand Supply Co, 1212 N 8th St, Sheboygan · verified Sep 13
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    Explore a nature-inspired approach to collage in a Forest Floor themed class. Build textured compositions with hand dyed paper and fabric, strips of silk, cheesecloth, and other elements, then finish your pieces with simple embroidery stitches. The experience is intended to be creative and relaxing, and all materials are provided.

    Event website ↗
Thursday, October 22 1 event
  • 6pm

    16 SPOTS LEFT! Oct 22nd - LushLOUNGE Chunky Knit Blanket Workshop

    LushLOUNGE, 1210 Michigan ave, Sheboygan · verified Sep 13
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    Settle in for a relaxed, hands-on workshop where cozy chunky knit blankets come together alongside delicious drinks and food. It is beginner friendly and great for seasoned crafters too. You will create your blanket using only your hands, head home with your finished piece tucked in a blanket bag, and leave with a new skill. Afterward, expect emailed instructions and yarn shopping tips for future projects. Blankets typically begin as lap throws and often grow to full-body size. Choose a looser or tighter style, which affects dimensions. The tightest approach makes a blanket about 45 by 42 inches, and most end up larger. Preregistration is required and seating is limited on a first come, first served basis. Two pricing options are available. The $65 option lets you pick from the yarn colors brought to the workshop. The $85 option lets you preselect premium yarn that is softer and thicker, helps hide imperfections, and offers many color choices. For that option, you will choose one or two colors via email about four weeks beforehand. Registration for the $85 option closes four weeks prior if not sold out, and the $65 option closes two weeks prior. There are 18 spots available. Participants ages 12 and up can complete a blanket on their own. If you want the social experience without the knitting, an optional $35 add on will have your blanket finished and ready for you at the workshop, and it must be purchased at least two weeks in advance. This add on applies only to the $85 registration. For last minute changes due to illness, injury, or schedule conflicts, reach out as soon as possible to see if adjustments can be made.

    Event website ↗
Saturday, October 24 3 events
  • 8am

    The Landjager Cup at Road America

    Road America, Plymouth · verified Sep 13
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    The Landjager Cup features an 8 hour and 7 hour enduro at Road America. The entry fee is $1,950, and an early payment discount of $200 is available. Participation is limited to 80 cars. For registration questions, contact reg@champcar.org.

    Event website ↗
  • 8:30am

    2026 Halloween Disc Golf Challenge @ Road America

    Road America, Plymouth · verified Sep 13
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    A Halloween-themed disc golf challenge takes over Road America, blending precise throws with the high-octane atmosphere of track racing. The event uses a flex-start format so players can begin within a set window, bring their own cardmates, or arrive solo and be placed with a group. Cards must have at least three players to start. This year’s format allows competitors to use their own bags and throw their favorite plastic. Players in divisions such as Pro, Bro, Fun, Wom, and Jrs receive a custom event-stamped Road America disc from the Paddock Shop. Cash prizes are offered in every division, with an added $10 per registered woman going directly into the women’s purse. All entrants are included in random drawings for bonus discs and premium items. Costumes earn an extra entry into a special raffle, and an on-site fly mart will offer a wide selection of premium discs and gear throughout the day.

    Event website ↗
  • 7pm

    Ryan Mendolla Appears at Rumors Roadhouse

    N7454 Summit Road, Plymouth, WI, United States, Wisconsin 53073, Plymouth · verified Sep 13
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    Appleton-based instrumental guitarist Ryan Mendolla performs at Rumors Roadhouse with a set that blends contemporary folk, pop, and blues, combining original compositions with reimagined favorites from the last five decades. His guitar work reflects influences like M. Ward, Lindsey Buckingham, and Jeff Tweedy, delivering melodic interpretations alongside his own material.

    Event website ↗
Tuesday, October 27 1 event
  • 5:30pm

    ACOTAR 6 Release Party

    Sip&Story LLC, 507 Broadway Street, Sheboygan Falls · verified Sep 13
    Free

    Celebrate the release of ACOTAR Book 6 at Sip&Story LLC with a gathering devoted to the world of Prythian. The event features themed drinks available to buy, snacks, and opportunities to connect with other fans of the series. Admission is free. Costumes are encouraged, whether you choose a favorite character, a member of a court, or attire inspired by the setting. Wings, crowns, elegant gowns, or leathers are all welcome.

    Event website ↗
Wednesday, October 28 1 event
  • 7:30pm

    Specters of the Spotlight Ghost Tours

    Weill Center for the Performing Arts, 826 N 8th St, Sheboygan · verified Sep 13
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    After dark, the tradition of the ghost light takes on meaning in this nearly century-old theater where flickering bulbs and unexplained footsteps have long been reported. Specters of the Spotlight Ghost Tours presents a 90-minute guided experience that blends compelling stories with behind-the-scenes access. Guests hear accounts of former performers and unusual happenings, step into backstage spaces rarely open to the public, feel the energy from the haunted balcony, and stand onstage in the glow of the ghost light. The experience suits history enthusiasts, theater fans, paranormal investigators, and the simply curious, though it may not be appropriate for children. Cameras are encouraged... an unexpected photobomb is always possible. A cash bar will be available, and beverages may be enjoyed during the tour. Doors open 30 minutes before the start, and a brief intermission is included. Tickets are $20 per person plus fees, and advance registration is required at least 24 hours ahead. Some areas are not fully ADA accessible; for accommodation requests, contact the Weill Center at (920) 208-3243. Paranormal investigative devices are welcome.

    Event website ↗
Thursday, October 29 2 events
  • 3pm

    Dementia Caregiver Support Group

    220 Haven Dr, Sheboygan Falls · verified Sep 13
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    Pine Haven’s Dementia Caregiver Support Group provides a warm, judgment free setting for caregivers to connect with others who understand, share experiences, and find encouragement. Attendees can explore practical caregiving strategies and learn about helpful resources with guidance from professionals. It is intended for anyone seeking support, answers, or simply a place to be heard. The group is free, open to the public, and does not require an RSVP.

    Event website ↗
  • 6pm

    Open Mic Night @ Paradigm Coffee & Music

    Paradigm Coffee and Music, 1206 N 8th St, Sheboygan · verified Sep 13
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    Paradigm Coffee and Music hosts an open mic night held most months. Musicians and poets can sign up before performances start, then take the stage for short sets. The room is set up with bass and guitar amps, so performers can plug in and play. Music slots are typically limited to up to two songs, while poetry readings are briefer. Stand-up comedy is not part of the program. Please avoid using the mic as a soapbox, and help keep things smooth so no extra rules are needed.

    Event website ↗
Friday, October 30 1 event
  • 2:30pm

    Glow In the Dark: Pottery Class🧪

    811 New York Ave, Sheboygan · verified Sep 13
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    Create a glow in the dark ceramic piece at this beginner friendly class at MAS Arts Studio. Design a statement bowl, a memorable mug, or a one of a kind planter while working under blacklight. Instructors provide step by step guidance, and registration covers clay, tools, instruction, glazing, and kiln firing. Bring your imagination and leave with a handmade piece ready to display for years to come.

    Event website ↗
Saturday, October 31 1 event
  • 9am

    Greenbush Trick or Trail 5K/10K

    Greenbush Recreation Area, Glenbeulah · verified Sep 13
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    The Northern Kettle Moraine Nordic Ski Team hosts the debut Greenbush Trick or Trail 5K/10K on the Greenbush trail system in a scenic setting. Participants can select a 5K or 10K route that showcases the natural beauty of Kettle Moraine, with hilly stretches and rugged paths. It suits runners chasing a personal best as well as those simply looking to enjoy time on the trails.

    Event website ↗
Sunday, November 1 1 event
  • 4pm

    Cinderella by The United European Ballet in Sheboygan, WI

    Weill Center for the Performing Arts, 816 Niagara Ave, Sheboygan · verified Sep 13
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    The United European Ballet Company brings Cinderella to the Stefanie H. Weill Center for the Performing Arts for one night only. This ballet tells a story of magic, romance, and transformation as a kindhearted young woman sees her fortunes change, moving from hardship to a royal ball and a dream fulfilled. Set to the music of Sergei Prokofiev, the production features expressive choreography, striking costumes, and an international cast of dancers. Seating is limited.

    Event website ↗
Thursday, November 5 4 events
  • 9am

    Sheboygan November Meetup: Caffeine & Cashflow | Networking for Full-Time Investors

    Field to Fork, 505 S 8th St, Sheboygan · verified Sep 13
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    Billed as the largest real estate investor networking gathering in Wisconsin, this morning meetup at Field to Fork is all about conversations and connections. It is entirely focused on networking, with no pitches, no set agenda, and no sponsors. Real estate investors, full-time professionals, business owners, entrepreneurs, and other high performers come together to exchange ideas and fuel growth. Attendees are encouraged to arrive with an open mindset and share what they are working on, where they excel, and one area where support would be helpful. Free parking is available in the back, and the group meets in the bar area located between Field to Fork and Il Ritrovo, which are connected buildings. The Sheboygan gathering happens on the first Thursday morning of each month. Additional monthly meetups take place in Green Bay, Appleton, La Crosse, Delafield, Milwaukee, and Watertown. A Facebook group called Caffeine & Cashflow Business Networking offers updates, space to share insights, and ways to stay connected between events.

    Event website ↗
  • 3pm

    Infinite Boundaries Retreat | All Stages All Ages

    The Osthoff Resort & Spa, 101 Osthoff Ave, Elkhart Lake · verified Sep 13
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    Designed for women of all ages who have faced breast cancer, this four day retreat at The Osthoff Resort & Spa centers on renewal, connection, and a return to personal strength and hope. Participants can look forward to uninterrupted time for themselves, restorative pampering, and heartfelt conversations with others who understand the journey. The experience blends creative and expressive activities that support healing, peaceful moments in nature, and nourishing meals, with ample opportunities for reflection, laughter, and meaningful connection. The registration fee is $450 and includes a private room, all meals, and activities. A $150 nonrefundable deposit reserves a place, with the remaining balance due one week prior. Thanks to donor support, each attendee receives a significant scholarship, as the actual cost is about $1,600, and financial concerns should not be a barrier to attending.

    Event website ↗
  • 5pm

    Holiday Kick Off Pop Up

    Restoration Gardens, Sheboygan Falls · verified Sep 13
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    The holiday season kicks off in the Christmas Barn at Restoration Gardens, decorated for the season. This pop up features a variety of vendors, the Harvest Street food truck serving food, and samples from participating sellers. Heirloom apple cider will be available, and demonstrations will showcase ideas for holiday decor and entertaining. Additional details and vendors will be announced.

    Event website ↗
  • 7pm

    The Play That Goes Wrong: High School Edition

    Plymouth High School Auditorium, Plymouth · verified Sep 13
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    Plymouth High School Drama presents a high school edition of The Play That Goes Wrong, a backstage and onstage comedy of errors wrapped around a 1920s whodunit. The story centers on the Cornley Polytechnic Drama Society as they attempt to stage The Murder at Haversham Manor. Director Chris Bean welcomes attendees while the company rushes to finish an incomplete set, then the performance begins despite the scramble. Charles Haversham is found dead and the investigation starts, yet the production quickly unravels. Jonathan stumbles in on his first entrance. Thomas and Perkins struggle with a door that will not open. Props vanish, actors are nowhere to be found, pieces of the scenery give way, lines are missed or mangled, and performers slip out of character as the turmoil spreads from backstage to center stage. Even so, Inspector Carter presses on with the case. As the mishaps build, the suspense becomes whether the culprit will be revealed or whether the troupe can simply make it to the end of the show.

    Event website ↗
Saturday, November 7 5 events
  • 9am

    Craft and Vendor Showcase

    300 Riverside Cir, Plymouth · verified Sep 13
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    Celebrate the inaugural craft and vendor showcase organized by RAPT, the Riverview Middle School parent and teacher group. This community gathering spotlights local makers and vendors while raising funds that directly support middle school students. Spend the day browsing unique goods, connecting with neighbors, and showing school spirit as the first edition of this event gets underway.

    Event website ↗
  • 9am

    8th Annual Holyland Holiday Extravaganza

    911 Main St, St Cloud · verified Sep 13
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    Kick off your holiday shopping at a community marketplace featuring raffle baskets and a wide range of local vendors. Browse skincare, home goods, handmade crafts, bakery treats, floral arrangements, wreaths, glass art, cookies, and more. Confirmed participants include representatives for L'BRI, Avon, Tupperware, Norwex, Scentsy, Pampered Chef, and Nails With Rose, along with Brim Haus, Crafts by Sandy, Perfectly Imperfect, Hickory Road Creations, Glass by Barb, Bellissimo Skincare, Easy Peasy Creative Co., Holyland Corner Bakery, Wish Me A Rainbow Cookies, and floral creations by Nancy Grams. Proceeds from all raffle baskets will support an area organization or a family in need. For vendor availability, communication is handled only by Denise Meyer or Angie Steffes, and messages from anyone else are not authorized and may be scams.

    Event website ↗
  • 9am

    Light Up The Holidays At The Linhay

    W4907 Hilltop Road, Fredonia, WI, United States, Wisconsin 53021, Fredonia · verified Sep 13
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    Celebrate the season at The Linhay with a thoughtfully curated holiday shopping experience. Explore distinctive gifts in an elegant, cozy setting that makes checking off your list feel effortless. While browsing, you might spot the resident peacocks looking regal amid the frost. Vendors interested in participating can email Ashley at explorewithbooks6@gmail.com.

    Event website ↗
  • 10am

    Winter Wonderland Watercolor Class

    826 S 8th St, Sheboygan · verified Sep 13
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    Explore the quiet charm of winter landscapes in this watercolor class led by Cindy Sarkady. Learn to layer transparent washes, blend smooth gradients, lift pigment to reveal light, and add delicate touches that suggest falling snow and crisp detail. The atmosphere is easygoing and encouraging, making it a good fit for first-time painters and seasoned creatives who want to play with cool seasonal palettes and luminous effects. All materials are provided, though you are welcome to bring your own favorite brushes and paints. Please bring a couple of reference photos to work from, and additional references will be on hand. The fee is $45.

    Event website ↗
  • 4:30pm

    2026 Steak Fry

    Silver Creek Fire Department - Sheboygan County WI, Random Lake · verified Sep 13
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    Silver Creek Fire Department in Sheboygan County, Wisconsin hosts its annual steak fry featuring charcoal grilled rib-eye steak dinners. Each dinner costs $30, and kids meals are available for $5. Dinners are available by advance ticket only, with no sales at the door, and tickets can be purchased through any SCFD member. A bar will be available, and the event features live music by Myles Wangerin and raffles. Those not attending the dinner can still enjoy the drinks, music, and raffles.

    Event website ↗
Friday, November 13 1 event
  • 12pm

    Festival of the Trees by Tamarisk at Camp Y Koda

    YMCA Camp Y-Koda, Sheboygan Falls · verified Sep 13
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    Festival of the Trees by Tamarisk fills the main lodge at YMCA Camp Y-Koda with the sights and sounds of the season. Decorated Christmas trees, wreaths, centerpieces, nativities, and snow globes contributed by local individuals, businesses, and organizations are displayed and offered in a silent auction that supports designated beneficiaries in the community, including an individual in need and or a local nonprofit organization. Local musicians perform holiday favorites as visitors explore a marketplace featuring creations from area artisans. An outdoor lighted walk through the woods extends the festivities outside, with food and warm festive cocoa or grog available. Cap the visit by picking up holiday sweets to take home, for a celebration that blends giving back with classic Christmas traditions.

    Event website ↗
Saturday, November 14 2 events
  • 9am

    Sheboygan South High Booster Club Craft and Vendor Fair

    Sheboygan South High School, Sheboygan · verified Sep 13
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    Taking place at Sheboygan South High School, the Sheboygan South High Booster Club Craft and Vendor Fair features a wide range of local crafters and small businesses offering handmade items, unique seasonal gifts, and decorations. Raffles will be available, and concessions will be offered throughout the day. Admission is $2. The event creates a warm, community-focused atmosphere with plenty of opportunities to start holiday shopping while supporting local makers.

    Event website ↗
  • 10am

    Reindeer Village 2026

    SoLu Estate Winery, Cascade · verified Sep 13
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    At SoLu Estate Winery, the second annual Reindeer Village transforms the grounds into a festive celebration of reindeer and Scandinavian traditions. Spend time with the herd during photo opportunities, meet them in designated areas and chat with knowledgeable handlers. Learn more through education sessions that include sleigh pulling demonstrations, and opt into reindeer walks through the vineyard for an additional fee. Around the property, enjoy toy making with Santa and his elves, a recreated Viking village with live reenactors, live music on select days, ice sculpture carving and glass blowing on select days, a holiday market featuring local artisans, Scandinavian food and beverages, face painting and festival hairstyling, Nordic storytime, a selfie station and plentiful photo backdrops. Camel rides are also available for an extra charge. The event features expanded offerings and thoughtful surprises throughout.

    Event website ↗
Thursday, November 19 1 event
  • 6pm

    Nov 19th- LushLOUNGE Chunky Knit Blanket Workshop

    LushLOUNGE, 1210 Michigan ave, Sheboygan · verified Sep 13
    See details

    Settle in for a relaxed, hands-on chunky knit blanket workshop with food and drinks to enjoy. Beginners and seasoned knitters are welcome, and no needles are needed since blankets are made entirely by hand. Participants finish the evening with a completed blanket tucked into a blanket bag and a new skill, plus emailed instructions and yarn shopping tips for future projects. You can choose a loose or tight style, which affects size. The tightest stitch creates a blanket around 45 by 42 inches, and most turn out larger. This is a pre-registered event with limited seating on a first come, first served basis, and there are 18 spots available. Two pricing options are offered. The $65 option lets you select from the yarn colors brought to the workshop. The $85 option includes advance color selection in a premium, softer and thicker yarn that helps disguise small imperfections, with the chance to choose one or two colors after an email sent about four weeks before the session. If not sold out, the $85 registration closes four weeks prior and the $65 registration closes two weeks prior. Ages 12 and up can complete a blanket independently. If you prefer the social experience without the knitting, an optional $35 add-on will have your blanket completed and waiting for you. Purchase the add-on at least two weeks in advance. It can only be added to an $85 registration.

    Event website ↗
Friday, November 20 1 event
  • 4pm

    Kohler Holiday Market

    419 Highland Dr, Kohler · verified Sep 13
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    This event takes place at the American Club in Kohler, Wisconsin.

    Event website ↗
Saturday, November 21 2 events
  • 6pm

    John Gay at Conrad’s 2nd Knot

    Conrad’s 2nd Knot, 19133 County Road XX, Kiel · verified Sep 13
    See details

    https://johngaymusic.com/home

    Event website ↗
  • 7pm

    Michael Murphy appears fireside

    Rumors Roadhouse, Plymouth · verified Sep 13
    See details

    Michael Murphy brings an inventive, emotionally charged approach to the blues at Rumors Roadhouse. Rooted in the genre’s feeling yet bold in delivery, he blends time-honored influences with surprising twists for a sound that is both familiar and fresh. His performance channels passion and craft into vivid musical colors, carried by the resonance of wood and steel and the strength of his voice.

    Event website ↗
Saturday, November 28 2 events
  • 9am

    Small Business Saturday Holiday Market

    1500 Douglas Dr, Plymouth · verified Sep 13
    Free

    Hosted by Generations and TLG Botanicals, this third annual holiday market celebrates Small Business Saturday with free admission and a focus on local shopping. Explore up to 40 vendors throughout the venue, including crafters, local businesses, and more, and check off your holiday gift list. Pic A Deli will be available during the lunch hour with a selection of food. For questions or vendor information, email tlgbotanicals@gmail.com. Generations and TLG Botanicals are the only organizers for this event, and vendor applications should not be sent to anyone else.

    Event website ↗
  • 2pm

    All @ Once at Solu Estate Winery

    SoLu Estate Winery, Cascade · verified Sep 13
    See details

    All @ Once brings a laid-back acoustic performance to Solu Estate Winery, highlighting a mother and son duo with easy chemistry and smooth vocal harmonies. The set features pop-rock favorites alongside enduring classics, delivered with an intimate, unplugged feel that pairs well with a glass of wine and a scenic backdrop. Lindsey, also a vocalist with Jupiter Lynx, performs with her son to blend experience, connection, and heartfelt energy into an inviting live music set.

    Event website ↗
Thursday, December 3 1 event
  • 9am

    Sheboygan December Meetup: Caffeine & Cashflow | Networking for Full-Time Investors

    Field to Fork, 505 S 8th St, Sheboygan · verified Sep 13
    See details

    A statewide real estate investor networking series now meets in Sheboygan for a morning focused entirely on connections and conversation. There are no pitches, no set agenda, and no sponsors, creating space for meaningful, business-building dialogue among full-time investors, entrepreneurs, business owners, and other high performers. Attendees are encouraged to arrive ready to discuss what they are working on, the strengths they bring to the table, and one area where support would be valuable. The group gathers in the bar area situated between Field to Fork and Il Ritrovo, which are connected, and free parking is available behind the building. This Sheboygan meetup recurs on the first Thursday morning of each month, with additional monthly gatherings in cities such as Green Bay, Appleton, and Milwaukee. Updates and ongoing connections are shared in the Caffeine & Cashflow Business Networking Facebook group, and the community emphasizes collaboration over competition.

    Event website ↗
Saturday, December 5 2 events
  • 1pm

    An Old Farm Country Christmas Book Talk

    W7965 State Highway 23, Greenbush, WI, United States, Wisconsin 53026, Glenbeulah · verified Sep 13
    See details

    Celebrate the spirit of Wisconsin holidays at Wade House with a book talk featuring Susan Apps-Bodilly, co-author of Old Farm Country Christmas with her father, Jerry Apps. Through memories from farmhouse kitchens, one-room schoolhouses, rural churches and snowy fields, the program shares traditions, recipes, photographs and illustrations from Midwestern Christmases spanning the Great Depression to the 1950s. A Q&A and book signing will follow in the Wade House Visitor Center Walnut Room, then sample tastings and a craft activity inspired by the book will be offered at the historic Stagecoach Inn. An advance community screening of PBS Wisconsin’s Jerry Apps: Home for the Holidays will be presented later at no cost, with a $2 donation encouraged. Copies of Old Farm Country Christmas will be available, featuring more than 80 family recipes, 12 nostalgic craft projects, 50 vintage images and many stories of farm holiday life. Admission is $8 for adults ages 18 to 64 and for teens ages 13 to 17, $6 for seniors 65 and over and for children ages 5 to 12, and free for children under 5. Advance registration is required. Society members receive a 10 percent discount. Set within the restored Wade House, a 27-room Greek Revival stagecoach inn once situated along a well-traveled route between Fond du Lac and Sheboygan, the site is a Wisconsin Historical Society property featuring a blacksmith shop, a sawmill and the Wesley W. Jung Carriage Museum, home to the state’s largest collection of carriages and wagons, with horse-drawn wagon rides linking the visitor center and historic core.

    Event website ↗
  • 1pm

    Run, Santa, Run Sheboygan at Blue Harbor Resort

    Blue Harbor Resort, 402 Beachfront Dr, Sheboygan · verified Sep 13
    See details

    Blue Harbor Resort transforms into a festive setting for the Run Santa Run 5K, a spirited celebration where holiday characters take center stage. Runners and walkers fill the streets of Sheboygan in Santa and Elf outfits and other wintry looks, spreading cheer with every step. Along the route, participants encounter playful aid stations, a visit from Santa Claus, and a lighthearted mission to keep the Grinch from spoiling the fun. Participants can choose to run or walk as Santa, Elf, or Penguin, with character shirts, hats, or accessories available to help complete the look. The experience is designed for all ages and mixes friendly competition with plenty of seasonal joy. After crossing the finish line, the festivities continue with a North Pole themed post race party at Blue Harbor Resort.

    Event website ↗

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